This invention relates to new bis-N-aminoimides and their preparation; polymers derived from the new bis-N-aminoimides; and polyimides having an N-N linkage and their preparation; the invention is also concerned with new diimides.
ii) Description of Prior Art
In a study of chemiluminescent organic compounds H. D. K. Drew and H. H. Hiatt (J. Chem. Soc. 16, (1937)) found that the reaction of hydrazine with phthalic anhydride can yield the N-aminophthalimide as well as phthalhydrazide: ##STR3##
A maximum yield of about 50% of N-aminophthalimide was obtained when the reaction was carried out over a short period of time, and this readily converts to phthalhydrazide. They found that N-aminophthalimide reacts with phthalic anhydride in almost quantitative yield to give the diimide which is a stable compound, mp 311.degree.-313.degree. C. ##STR4##
Subsequently they reported (H. D. K. Drew and F. H. Pearman, J. Chem. Soc. 26, (1937); H. D. K. Drew and F. H. Pearman, J. Chem. Soc. 586, (1937)) that with substituents in the 3- and 6-positions (a. 3-chloro, b. 3,6-dichloro, c. 3-amino-, d. 3,6-diamino-) that the N-aminophthalimide could be selectively formed. Presumably with substituents flanking the imide moiety and providing Some steric hindrance the 5-membered ring in the N-aminophthalimide is preferred.
Later it was found (F. G. Baddar, M. F. El-Newaihy and M. R. Salem, J. Chem. Soc. 838, 1969) that in the reaction of 1-phenylnaphthalene-2,3-dicarboxylic anhydride (R.dbd.H in formula (XXX)) ##STR5## with hydrazine that a mixture of the N-amino compound and the phthalazine-1,4-dione were obtained. The 4'-7-dimethoxy anhydride (R.dbd.OMe) however gave the N-amino compound.
It has also been reported (M. S. Aleziou, V. Tychopoulos, S. Ghorbanian, J. H. P. Tyman, R. G. Brown and P. I. Brittain, J. Chem. Soc. Perkin Trans. 2, 837 (1990)) that hydrazine reacts with 4-nitro-1,8-naphthalic anhydride to give the N-amino compound: ##STR6##
Polyimides are an important class of polymers noted for their exceptional thermal stability and solvent resistance. They are commonly synthesized by the reaction of dianhydrides with aliphatic or aromatic diamines. For example, Kapton.RTM. is synthesized from pyromellitic dianhydride and oxydianiline ##STR7## and Ultem.RTM. is synthesized from bisphenol A dianhydride and m-phenylene diamine: ##STR8##
It is desirable to produce polymers of high glass transition temperature, especially such polymers which are soluble, so that polymer films and coatings of high glass transition temperature polymers can be produced from solution.